


Fetish & Fantasy

by GavinIsaNuisance



Series: Shemales Topping Sissies [3]
Category: Original Work
Genre: Anal, Anal Fingering, Anal Sex, Butt Plugs, Cheerleader, Clothed Sex, Cock & Ball Torture, Cum on Ass, Dildos, Escort Service, F/M, Femdom, Feminization, Futanari, Futanari on Male, Gen, Handcuffs, Humiliation, Jock Straps, Masks, Pegging, Photo Shoots, Public Humiliation, Public Sex, Shemale on Male, Spanking, Spitroasting, Strap-Ons, Threesome - F/F/M, blowjob, pimped out, sissification, sissy, sissy maid
Language: English
Status: In-Progress
Published: 2020-06-27
Updated: 2020-06-27
Packaged: 2021-03-03 19:08:47
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 9,824
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24940600
Author URL: https://archiveofourown.org/users/GavinIsaNuisance/pseuds/GavinIsaNuisance
Summary: An aspiring model Terry Kilkenny gets the role of a lifetime, to pose in nude and sexual photos for an experimental fetish website, only to discover his humiliation was made as an advertisement for an escort service for shemales! Now Terry becomes a pimped out sissy to hot trannies by his domineering boss
Relationships: Terry/Claudia/Ramona, Terry/Lana (Shemale)
Series: Shemales Topping Sissies [3]
Series URL: https://archiveofourown.org/series/1793206
Kudos: 35





	1. The Price of Fame

**Author's Note:**

> This work and everything therein is entirely fictitious. Any similarities to persons or things living or dead is purely coincidental and entirely unintentional. All persons depicted in nude/sexual nature are 18 and up.

This story takes place in the cesspool that is Los Angeles, California. Those familiar with my work know I've ranted far and wide about how miserably mismanaged and discouraging this town is so I'll spare the tirades and move onto the story.

The gig economy is the lifeblood of many millennials and 'zoomers' trying to find independence while staking their claim in the many entertainment industries in the city of homeless angels. These jobs are typically work as you go, despite legislature to reform that. You can also quit at any time and start back at any time. It's the perfect faceless hustle for those who want something more secure.

One Massachusetts transplant would love nothing more than to find his place in this dog-eat-dog world of narcissism and pretentiousness. This former arts major is Taran Kilkenny, a twenty-one year old graduate, independent liver, and aspiring model. He typically went by Terry, because people could spell it easier. Terry was from Quincy, Massachusetts, one of those uppity Boston area suburbs filled with everyone who made the leap forward from Bean-town.

Terry was a communications major at Tufts University, who realized at a young age he was desperate for fame, even though he was smart enough to graduate a year early. He couldn't act, he couldn't write, and he didn't have the patience to learn the technical aspects of film work so he decided he wanted to be a male model. He certainly took care of himself. He was slender but not too spindly, flat chest with budding abs, a very baby face, red hair that he usually styled up, decent lowers, but with wide hips, having an exceptional rear end. His dick was nothing special, average size, not too big, not too small. Terry aspired to be one of the always half naked Calvin Klein models who typically have nothing on other than briefs.

The problem is, all aspects of the entertainment world are based in connections, and a college degree is worthless without them. Terry soon realized he wasn't studly enough to be a Calvin Klein model...or any modeling for that matter. He never stopped trying though, but he typically had little offers as his greatest assets were...well, his ass—ets. This meant his pool of modeling in the buff was limited unless he worked out more, which Terry desperately tried to do.

Usually discouraged, Terry made his living with various gig app jobs around LA considering his limited range of practical skills and life experience...and he really just wanted to make money while fruitlessly trying to make connections. Post-COVID, LA was starting to open back up and the night life was starting to return to normal yet again.

Terry worked weekend nights as a ride share driver, as there were many drunk people around LA who wanted to get home without endangering the lives of others, which always made for interesting taxicab confessional conversations. Terry was driving two very drunk girls home from a fancy West Hollywood club.

He fancied himself a ladies man, but typically struck out with women, especially when moving to LA. He found LA girls stuck up, pretentious, superficial, and airheaded...yes, all those stereotypes were true.

The one girl was blonde with her hair in a bun, but a sexy bun that wants to have fun. She had blue eyes and wore a jean jacket over a cocktail dress, despite it not being cold outside. The other woman was African-American with long wavy hair. She had a stud in her nose and wore a midriff and a skirt. Both women wore high heeled boots and were in their mid-twenties, perhaps a few years older than Terry. Both were chuckling like loud bitches that drank too much at the club.

"He was so checking you out, Claud" the blonde said.

"No way, it was the dude behind me, you didn't catch those signals, total gay boy." Claud, or rather, Claudia interjected.

"Oh my God, I totally didn't notice."

"It sucks, the gays always dress the best, they're super cut, they're nice, but they're into each other."

"We gotta hit up this club in Echo Park. My sister says its dope, no scrubs."

"No scrubs?"

"And tons of thirsty dudes."

"Oh my God, Ramona, that fucking guy I was texting, the accountant, look at this" Claudia showed the other girl: Ramona, her phone. Terry looked in his rearview and saw it was an obvious dick pic, and it wasn't all that impressive.

"Yuck" Ramona winced.

"I am so sick of these fucking—and by the way, I am ninety percent sure he's married" Claudia added. The two then noticed Terry just sitting and driving and figured they should say something as they did just open up a dick pic in his car.

"How's your night going sir?" Claudia asked.

"Fine" Terry said, note a lack of a Boston accent. "Clubbing, huh?"

"Yeeeeeah, getting drunk with this bitch and grinding on hotties" Ramona shrieked, sticking her tongue out, revealing a stud in her tongue.

"Cool. How's uh, how's the dating game?" Terry asked.

"Well if you could hear our very loud conversation—" Claudia began.

"We're sorry about that by the way" Ramona added.

"It sucks. Sorry for opening this up in your car" Claudia put her phone away.

"It's fine, I couldn't help but look, it's uh, not that impressive" he said sure of himself.

The two girls snorted. "I mean, it's pretty big" Ramona said.

"Yeah I was just saying this motherfucker is classless and childish, but he's got a nice dick."

"T-that's average size. At best" Terry added, digging himself in a deeper hole of awkward.

"Average my ass, that's a ten inch dong, easy" Claudia snarked. "Easy!"

"Yeah and look at those thighs, that bitch takes care of himself" Ramona piled on.

"My pussy is screaming just thinking about it. If this asshole wasn't a man-child who probably has a child I'd be jumping on that dick morning, noon, and night!" Claudia chuckled.

"Well if you don't want him, give him my number" Ramona pleaded. "Fuck his family, that cock's too good to ignore."

"It doesn't look that big to me." Terry interrupted, not knowing when to shut up.

"Whoa. Hold up a sec, seriously, what do you know about big dicks?" Claudia asked.

"You see a lot of dicks?" Ramona added.

"Well, I know my own dick. I'm just saying."

The girls laughed. Terry blushed in embarrassment, wishing he hadn't said that. Why oh why did he have to say that? As if these two hot chicks were gonna jump all over him in the middle of a random street in The Westside.

"N-Nevermind."

"You know, guys who comment about the size of other guy's dicks, usually got tiny cocks themselves, just saying" Ramona sneered, which stung.

"I mean, were you like, trying to hook up with us?" Claudia asked. "Nothing personal, but I want my man to grab me and throw me on the bed, can you even lift me up? I don't weigh that much."

"Uh y-yeah, of course I could" Terry stammered, again the girls laughed. "And I got a big dick too."

Ramona snorted. "Okay."

"Is this your way of tryna' hook up with us? Cause if that's your game it's weak little boy" Claudia condescendingly said.

The rest of the ride was fairly quiet, well it wasn't but the topic of conversation didn't include Terry so it felt quiet for him, a terribly awkward and embarrassing kind of quiet. Sometimes the two were whispering instead of their yelling, Terry knew they were talking about him, probably texting or instagraming their friends telling them he's a total joke. The wannabe model sighed, wishing a proverbial semi would crash into them.

He dropped them off at their destination, surprise-surprise, another club. Claudia got out first, but Ramona waited a moment. "Hey, next time you wanna pretend to be a big man, remember this: guys with big dicks don't talk about their dick, they let the dick do the talking for them. Food for thought" she then left.

"I'll remember that" Terry groaned and slammed his head on the steering wheel.

Dejected, Terry continued to his next ride. It was getting late and he planned to call it quits, before getting one last call over his phone. It was for a lady in West Hollywood along the Sunset Strip, not going very far apparently. The name was Svetlana, she apparently had no profile pic on the app. Terry stopped by what he knew to be a modeling studio and was intrigued, forgetting the self-imposed humiliation of the last ride already. The woman had an hour glass frame, around early to mid-thirties wearing a very tight fitting pantsuit. Terry could see a giant bosom trying to desperately to break free of her bra, undershirt and gray blazer. Terry couldn't get a good view of her ass but he assumed it was amazing. She had sort of tan skin, blue eyes, and long jet black hair. She was on her phone when she got in Terry's Prius C.

"Nyet, this is unacceptable, Harriet!" the woman boomed in the thickest of Russian accents. "No, you get me someone else, and I need now! I need yesterday!" she boomed, but got off her phone "Da, Svetlana?"

"Uh, yeah" Terry nodded, and started the ride. He started along Sunset as per the GPS instructions while Svetlana continued to have a very loud phone conversation.

"No, Harriet! No, you listen!" Svetlana boomed. "Every model you send me is weak! They no show up, no stay late, they cannot deal with our website's mission. Unacceptable!"

Those words really put a smile on Terry's face. He listened in on the convo and it was obvious Svetlana was a talent manager or an agent of some sort.

"Nyet! Not Dillon, he too scrawny, too scrawny...not Tyler either, I'm not happy with these! I give you bottom line, get me new model by Tuesday or we're finished! Website is nearly up and running I need one last model, he must be centerpiece! Da, fine. Bye!" Svetlana hung up and threw her phone in her purse. "Sorry you heard that."

"No-no, it's quite alright, actually" Terry grinned. "You uh, you're an agent?"

"Among other things" Svetlana nodded. "I run website."

"Modeling, right?" Terry asked.

"Da, there is modeling involved, sure."

Terry looked at his GPS as they were turning onto Beverly Canyon Blvd, up in the hills above the famous city of Beverly Hills, their journey was almost over. Terry decided he had to ask, the worst she could say was no? Besides, nothing ventured, nothing gained.

He also figured a 'no' might set his self-esteem back by a lot considering the humiliation he suffered at the last ride. As he pulled up to Svetlana's house on a side street, he figured he had to ask.

"You know, I'm a model."

Svetlana got one brief look at Terry from behind her seat and scoffed. "Model for what?"

"You know, a model. I'm a male model. That's what you're looking for, right?"

Svetlana gave a scoff and a light chuckle. "You cannot handle this kind of modeling."

"Why not? Look I know what you're thinking; no I don't have any representation but—"

"No, I prefer models have no representation. I mean I look at you, and I see you cannot handle what I do."

"Why? What is it? Underwear? Swimsuit? I'm not camera shy" Terry insisted, trying to sell himself.

"Is nude" Svetlana said, very annoyed.

Terry blushed. Nude, huh? Well that threw the twenty-one year old for a loop, but still, he wasn't a prude. He knew this was part of the business, and he didn't mind the way he looked naked. While it was a bit out of left field, he still happily shrugged.

"So what?" he asked.

"Nyet. You don't want this job. Goodnight" Svetlana scoffed before just leaving.

"Wait but—" The door closed behind her and Terry watched Svetlana type a code into a gate box to open the barred gate to her mansion on the side of the hill. The boy watched her ass shake as she walked, revealing it was juicy and plump, just the way he liked it. Terry watched the gate close and took notice of the house number.

He was persistent, and a bit desperate. Those girls making fun of him had sparked a fire in the redheaded transplant. He wasn't gonna take this lying down. He apparently had all the qualifications they were looking for. He just had to better sell himself to the gatekeeper, that being Svetlana.

Terry returned to his studio apartment in North Hollywood's Noho Arts District which he was criminally overpaying for. It was a typical apartment, nothing special, just a mess. Now knowing Svetlana's house address, he knew this couldn't end on one 'no'. A tired Terry fell asleep, ready to be Mr. Persistent for a new day.

Indeed he spent the next day driving until around the afternoon when he decided to pay Svetlana a visit. No one seemed to be home. Terry tried to call the gate box, but again, nothing. As he was about to leave, another ride share drove up to the property, and to Terry's luck, Svetlana exited the car, Terry took a gulp and then a leap of faith. He left his car parked across the street and ran over to Svetlana just as the car drove away and before she could enter her gate.

"Hey, wait!"

"Da, who are you?" she asked.

"It's me, Terry—Taran, I was your driver last night?"

"Oh, da" Svetlana then looked at the boy up and down. "You look different in daylight. What you want. I am busy."

"Look, I know you told me last night you don't think I can model for you, but I'm here to tell you I'm the perfect candidate."

Svetlana rolled her eyes. "I don't have time for this."

"Wait! You said you want somebody without representation, I don't have it" Terry reminded her. "You need a nude model, I'm comfortable in my own skin."

"Is more than being nude. Besides, I need more than some...fair weather boy for website" Svetlana said coldly.

"I'm not fair weather! I don't even know what that means."

"This is no job, this is life choice" Svetlana warned him.

"It's the life I want! I wanna be a model!" Terry begged. "Do you want headshots? I got plenty in my car."

"No, no headshots. Trust me, you don't want this, I promise you. Good day" Svetlana opened her gate and started to walk again. Ever persistent, Terry didn't give up.

"What's your website? Can't I be the judge if I'm not right for it? You won't even tell me what it is!"

"Is experimental fetish website. Happy?"

Terry stopped in his tracks. Admittedly that threw him for a complete loop even though the nude element of the website should have thrown a few red flags his way. He looked quizzically at Svetlana for a moment, but she was already done with their conversation.

"Thought so. I say again: good day"

"Alright, I'll do it!"

Svetlana stopped. She turned around just as her gate closed, Terry was outside of it. "Is it like, porn or something?" he asked.

"Modeling is more tasteful...but it is like porn" Svetlana explained. "Is not easy. You look...weak and gutless. And I need weak and gutless but not your kind" she continued. "Your kind would run away at very sight of what I am doing."

"You don't know me" Terry defended, gripping onto the bars of the gate. Svetlana approached.

"One look at you, I say you run on first day shoot" she said.

"Try me. Gimme a chance to prove it to you."

Svetlana sighed. She made a face palm and looked Terry up and down again. She was intrigued giving the boy a second look, especially in better light. She sighed and walked right up against the gate.

"Turn round" she ordered.

"O-Okay" Terry agreed. He was completely against the gate.

Svetlana reached her hands from the other side of the bars and started to pat Terry down like he was being searched. She paid special attention to his hips and crotch area, where Terry became instantly aroused. Svetlana groped Terry's ass over his pants. She then moved to his front and loosened the belt he had on.

"What are you doing?" Terry asked.

"Inspecting you. You want job or not?"

Terry nodded, but before he could say another word Svetlana tore his pants and underwear down over his ankles, leaving Terry completely exposed in this public Beverly Hills street. Svetlana bent down and squeezed Terry's ass cheeks.

"Bend against gate." She ordered.

Terry gulped, doing as he was told. So this was the price of fame? He was now committing indecent exposure while this strange Russian lady groped and spread his most sensitive parts. He was intrigued at the fetish aspect admittedly, knowing this was a good way to break into to more experimental modeling, which would make him indispensable in the industry as there were models that had limits.

"Hairless" Svetlana nodded. Terry could tell by her tone that this was a good thing. "Is good. Only hair should be on head" she added.

Svetlana continued to spread Terry's ass, looking at his puckered pink and unspoiled asshole and was very impressed, happy he was persistent at his own behest. She reached around and played with Terry's cock, which grew from the tension and from being touched by this hot woman. The element of danger of being discovered on this street also turned them both on. Fortunately, this was a dead end residential street in the hills and there was no traffic while they did this.

Svetlana looked at Terry bending his ass over and resting against the cold metal bars of her gothic style gate to her luxurious Beverly Hills manor. She took out her phone and snapped a pic of his butt before she stood up, taking out a pack of Newport 100's. She shoved a cigarette into her mouth and used a Zippo lighter from another pocket to light it up.

"Good. You may dress" she commanded. Terry immediately pulled his pants up. He turned around.

"Well?" he asked.

"Must admit, you prettier naked than clothed. I need that. You can commit, da?"

"Absolutely. I can start now" Terry eagerly promised her.

"I need more. No headshots. I need other shots. Your ass. I want nude shots, all lowers, your dick, your legs, your tush. You can do this?"

"Y-Yeah, yeah. Of course."

"You know my modeling office?" Svetlana asked.

"Yeah-yeah, on the Sunset Strip."

"Bring me shots afternoon Monday, do not disappoint me" she ordered before walking to her home.

"Yeah! Uh, thanks so much by the way!" Terry called. Svetlana said nothing and walked into her house.

He drove home to The Valley as fast as the LA traffic would allow him to. Running and closing the door Terry grabbed a few things he needed: namely a DSLR camera and a tripod, and some studio lights. He quickly set up a makeshift photoshoot on his bed. Sensing everything was perfect, he tore his clothes off.

He set a timer on the camera and started to snap away. They started with him posing on his bed with his flaccid dick sticking up, then a few with him laying down with his legs in the air, and a few while he stroked his dick.

Next he wanted to focus on his ass, as it was obvious that was what Svetlana was interested in. He figured the site was merely a site for people with a booty fetish but he didn't really care, it would be something provocative that would give him an edge on other emerging models in the industry...little did he know...

Some photos were in a secretary pose, or with him lying on his side with his ass out. Some of these he would spread a cheek. Then he did some stand up shots with his ass sticking out, then some bent over. Finally he got on his bed and stuck his face down, spreading his cheeks with his hands and got a full shot of his ass. Terry figured these would be perfect enough for his new and seemingly demanding boss.

Monday came, and Terry spent his money to print the glossy photos he figured Svetlana desired, hoping not to turn any heads while he printed these at the local photoshop. He went over to the agency, paying the exorbitant fees for parking, and waited in Svetlana's office.

She sat at her desk and looked at the photos. Cigarette in one hand, photos in the other. Terry sat there and twiddled his thumbs, this was now or never. He figured if she didn't like these, there would be no second chances.

He heard Svetlana's muffled approvals, and assumed this was a good sign. She placed the photos on her desk and finished her cigarette, putting it out in a nearby ash tray. "You have no shame."

"Not much" Terry nodded.

"Good. Come here" she ordered. Terry walked behind her desk and Svetlana bent the boy over it. "Drop pants" she commanded. Terry didn't hesitate and they were quickly around his ankles, his ass sticking out. Svetlana groped his cheeks and gave them some pats and light spankings. "How shameless are you?"

"What do you need me to do?" Terry asked.

"You stick anything up your ass?" she asked.

"No" Terry blushed.

"You mind having butt plugs or dildos up your ass?"

Terry sighed of relief. He had reservations, but he'd rather they'd be plastic toys than a dude's cock, which was what he was worried about. "No, not at all."

"Good, cause modeling requires you shove dildo up your ass. You will expose asshole for camera, this okay with you?"

"Absolutely, whatever you need."

Svetlana smirked, and raised an eyebrow while she groped Terry's booty. "Whatever I need?"

"Yes, totally. I'll do it."

"Good then. You're hired."

"Oh thank you, thank you, thank you" Terry gushed. He was about to turn around but Svetlana forced him back onto the desk bent over.

"Stay there, step out of pants and underwear" she urged him.

Terry got stepped out of his pants and underwear and remained bent over and exposed while Svetlana left her office. Terry remained there and blushed, there was something sexual about being bent over his demanding new bosses desk. She returned moments later with a jock strap with a banana hammock for his dick. Terry blushed again as Svetlana placed the strap over his hip. "Perfect fit."

She got out her camcorder and started to shoot Terry's ass. "Shake your ass or me." Terry shook his moneymaker while Svetlana filmed him. "Good boy." She got up and close to him. "Spread cheeks."

Terry immediately moved his hands to his butt and spread them while Svetlana filmed his pink hole. Terry could instantly feel his dick hardening. He was s euphoric he didn't notice Svetlana stick her hands in a nearby jar of KY jelly. She moved two digits to Terry's asshole and Terry winced when the cold jelly coated his rim.

"Relax" Svetlana demanded.

Terry nodded, figuring this is what he signed up for after all. He tried not grunt when Svetlana slid a finger inside his hole, splitting it open and slicking up his insides. She swirled her finger around and Terry briefly moaned.

"You like? You like having finger inside your asshole?" she asked.

"Y-yes" Terry grunted.

"No-no-no, you love having finger inside your asshole."

"I love it" Terry said a bit more convincing, assuming this was part of a script. Svetlana smirked and shoved her second finger inside, blasting the boy's rectum with her two digits. Terry groaned again, but his ass was starting to open up and he blushed, this was admittedly pleasurable to him.

Svetlana shoved her fingers deep inside of him and caught some more soft moans coming from Terry, whose dick was rock hard. "Stand" she ordered. Terry obediently stood up, his dick leaking pre cum and now at full length. "Jerk your little cock."

Terry immediately stroked his member while Svetlana filmed him, still with her fingers in his butt. Terry moaned pleasurably aa he was close but he didn't know what he should do? If he came, it would be right on the desk.

"You close?" she asked

"Y-Yes" Terry moaned.

"Finish on desk" Svetlana ordered, answering that question.

Terry picked up his pace while Svetlana gave him a hand by shoving her fingers in deep. Terry gave one last grunt and shot a load of cum splattering all over the wooden desk. A few more shots and all that was left were drips.

"Good. Lick it up" she ordered

Terry raised an eyebrow. "But—"

"You want job?"

Terry nodded. Svetlana took her fingers out while Terry knelt down and ran his tongue along the desk and gulped down his salty load. Svetlana watched and filmed him while he licked the awkwardly tasting desk. Terry hoped he was the first person to be doing this. After he was finished, a satisfied Svetlana stopped filming.

"Very good. We start tomorrow. Come to my house. Twelve thirty, no later, I give you gate code you park in drive way, and wear strap" she instructed him before slapping him on the cheek.

Terry nodded and pulled his pants up.

He barely slept that night, wondering about the experience in Svetlana's office and while he hoped for more of that, he became a bit apprehensive due to the humiliating nature of it all...but it certainly turned him on.

The next day came, and Terry rushed over to Svetlana's manor, now having the gate code, he parked in her large driveway, arriving just before twelve thirty, he wanted to be as punctual as possible. He knocked on the door, and after a few moments, Svetlana answered.

"Good, you on time. Come-come" she ordered.

Svetlana grabbed him by the wrist and led him through her house. Terry was intrigued as to how the upper crust lived, but at the same time was mesmerized by Svetlana's ass as she dragged Terry. He got a boner from watching his demanding new boss for sure.

She took him to what was probably a converted office or den towards the back of the manor. It had many windows but they all had the blinds drawn. French doors led into it. And another set of French door sled to the backyard, which had a very nice pool and hot tub.

The room itself was set up like a photoshoot. There were many cameras set up on tripods and studio lights focused on a large California King sized bed. Several standing mirrors on the walls were situated to give the room a seductive look as well as having a completely mirrored ceiling. Towards the other side was an editing station with numerous monitors set up as some sort of a video village. Avid and Adobe Audio were simultaneously opened. Terry assumed that was where his work would be edited.

Svetlana closed the doors. "Okay, Taran, undress, leave the strap" she ordered.

"Okay. Oh, you can call me Terry, by the way."

She looked at him with scorn. "I'll call you as I see fit. But you call me Lana, understood?"

"Yes, totally" he said, disrobing.

"Good."

Svetlana, or rather, Lana, readied he cameras. There were a few columns, looking like they were stolen from The Acropolis situated on some of the walls. Lana got out a fancy fountain pen. "Bend over column" she ordered.

Terry nodded and picked a random column, bending his ass out. Lana walked over to him and pulled the jock strap down. She then dipped her pen and Terry winced as it was clear Lana was writing something on his ass. "Hold still!" she demanded, slapping his left cheek.

Terry clenched himself but eventually relaxed as the tickling of the pen wore off, he didn't want to look more like a bitch in front of his new boss. Lana finally finished and fetched a small mirror. "Finished. What you think?"

She positioned the two mirrors for Terry to get a look, the ink had just dried. In almost perfect calligraphy on his right cheek was PROPERTY OF FETISH & FANTASY. "Fetish & Fantasy?" Terry asked.

"Is website. Think of it as brand. Now then, we shoot, da?"

"Right, yeah" Terry pulled the jock strap back up.

"Good, first, lean on column again. Stick your tushy out."

Terry nodded. He leaned against the column and stuck his ass out. Lana started the cameras and filmed Terry in this most provocative of positions. Terry blushed knowing there was a camera capturing his nude booty that would be for the Internet to see.

"Good Terry, shake your ass" Lana commanded.

Terry smirked and shook his ass for the camera. He started with some basic shaking, then some twerking or at least as best as he could do, and then some flat out dancing of his butt for the camera, which impressed Lana.

"Excellent" she stopped the camera and got something from the bed. It was a black feathery eyes-wide-shut looking mask, or something you'd find at Mardi Gras or Fifty Shades of Grey. She put the mask over Terry's face. "So we see no see your face" Lana explained. Terry nodded. She restarted the cameras.

"Now, lower your strap slowly and turn your head" Terry made the seductive move while Lana filmed this up close with one of the cameras, filming up Terry's legs. "Excellent. Stick out tongue, and put finger in mouth" Terry did as he was told, looking like a true slut. "Yes, bad girl, Terry. Da, I like, I like!"

Lana then fetched something from a nearby table, a purple butt plug which she drizzled in a bottle of lube. She walked back over to Terry. "Stick this in your ass" she commanded.

Terry gulped, staring at the plug for a moment, but again, he knew what he signed up for. He took the plug and Lana went back to filming. Terry sensually spread a cheek with one hand while slowly putting the plug against his ass with the other.

He grunted as he pushed the plug through his sphincter. He grunted as his hole stretched to accommodate the plug. He managed to get it inside while Lana ordered him to play with the plug while she filmed.

Terry then went back to sticking his ass out with the plug inside of him. He pulled his jock strap up and down per Lana's instructions. He was sort of getting used to this, it was kind of hot.

"Okay, come to bed, stick ass out, face down" she ordered.

She filmed Terry seductively sauntering over to the bed and taking the desired position. First sticking his ass out before he shoved his hole face into the sheets and stuck his exposed rear up in the air, spreading his cheeks.

"You like it in your ass?" Lana asked.

Terry, assuming she merely meant the butt plug nodded. "Oh yes" he said seductively.

"You want more in your ass?"

Again in character, Terry nodded in the affirmative. "Yes, fuck my ass" he moaned.

"Good."

They took some more shots but Lana was satisfied. Terry took the plug out, which made his asshole gape and pucker. He put his clothes back on while Lana hand him a check. "This first day's pay. Good work."

Terry looked at the check, more than a month's rent. "Whoa."

"More where that came from. You come back tomorrow. I am done with you" she gave Terry a pat on his ass and he left, staring at the check in his hands.


	2. A Model Sissy

**Summary for the Chapter:**

> Terry continues his photo shoots where he meets two familiar faces who help feminize and fuck him for the shoot, where later Terry learns the truth about Fetish & Fantasy and begins his new life as an escort.

Over the next few days, Terry got his money's worth. He would pose in the studio in many provocative positions, almost always featuring his ass, and often with something phallic being shoved up there. Terry was working his way up from various butt plugs and was now onto dildos themselves, effectively training his rectum to take a cock.

Several occasions Lana would film Terry on location at several sketchy back alleyways in and around the Los Angeles area. They would feature him in similar poses with Terry enjoying the humiliation of having to shake his exposed ass in public. Each time, Lana would touch up the mark on his ass so it was always looking fresh.

Finally, though, one day, Terry came to the studio, and found two more cars there which was unusual. He went into the studio where he was again instructed to disrobe so Lana could touch up his ass brand. This day, Terry noticed a few items on the bed. It was the same mask he had been wearing, but this time there were a few outfits strewn out on the bed. Three, namely were a skimpy French Maid's outfit, a black and white striped prison uniform, and cheerleader outfit. The maid's outfit had the sexy black and white thong and corset, with a frilly too-short skirt, a pair of lacy assless panties with some silk stockings and high heels in Terry's size. There was also a black wig and matching maid's tiara. Completing the outfit was a sexy feather duster with a black dildo on the handle.

The cheerleader outfit was in blue with white and red trim around it. It was a short midriff and skimpy blue skirt. Emblazoned in red letters on the front of the uniform read: SISSY SLUT SQUAD. It came with a matching pair of tube socks. This one contained a blonde wig in pigtails.

The prison uniform featured a black and white striped tank top with matching booty shorts and long black and white striped socks. In red over the back of the booty shorts was: PRISON BITCH, GUILTY. The wig with this outfit was red and wavy.

"So...what's with this?" he asked nervously.

"For shoot today" Lana said finishing up. "You be sissy slut, we dress you up."

"We?"

"Da, we. I have help today. You better do as your told" she warned him.

On cue, two girls walked into the studio. Terry winced and went wide eyed when he saw them. Of course it was the two girls he gave a ride to and humiliated himself in doing so a week earlier: Claudia, and Ramona. He felt like Humphrey Bogart in Casablanca. Out of all the sissies, and all the girls, it had to be these two.

Unfortunately, they both remembered Terry. "Oh my God!" Ramona put her hand over your mouth.

"Weren't you...weren't you our driver? Oh my God, you were!"

"The one who was dick bragging" Ramona chuckled.

Terry sighed, and put his hands over his crotch. "Well come on, we gotta see your cock all day, you might as well show us how impressive it is" Claudia insisted. Terry turned to Lana.

"Well, go on. Show them your tiny cock."

Terry sighed and slowly moved his hand out of the way. Ramona immediately chuckled, Claudia seemed rather indifferent. "Huh, you know, it's not impressive, but I mean, it's not bad; I've seen way smaller—to be fair I came into this with the lowest expectations, though."

"No, that's a tiny cock for sure. Knew it" Ramona chuckled.

"Okay, we burning daylight, we turn Terry into sissy fuck slut, okay?" Lana insisted. "Come-come girls, get makeup."

"On it, Lana" Claudia promised her, holding up a portable makeup kit.

"We're gonna make this sissy shine" Ramona chuckled.

Terry sat on the bed and was humiliated by both women as they started to powder on concealer onto his face. They went with some rouge as well, some eyeliner, and some red lipstick. They first dressed Terry in the maid's outfit, slinging the tight dress on him before hooking on his mask and the wig with the maid's tiara. Terry blushed as he looked at himself in the mirror, mask on, glad no one could see his face.

"Okay, let's go. Terry stick out your ass for me" Lana commanded.

Terry leaned on the column and did similar poses that he did the other day and the days before, getting used to Lana's commands. Of course today he had two other people to contend with who definitely relished in Terry's humiliating feminization.

"Stick some fingers in your butt" Ramona commanded him.

"Yeah, embrace your inner sissy maid. Sissy maid's finger themselves" Claudia added.

"Do it, Terry" Lana ordered.

Terry posed more while licking two of his fingers and instantly shoving them up his ass, while the girls gleefully chuckled at his humiliation. Terry sighed but was getting used to this sort of treatment, it was a real turn on.

Next, Lana ordered Claudia to plug his asshole up with the butt plug while it was filmed. She snickered shoving the toy right into Terry's ass and he moaned loudly like a girl, which was perfectly caught on tape.

"Ooh, you like getting rammed, huh?" she asked.

Terry moaned. "Oh yes!"

Other shots included Terry using the feather duster prop to clean various surfaces around the studio while sticking his butt out to reveal that it was still plugged up. Lana made sure to capture every humiliating detail of Terry dressed in drag.

She got some good posing shots as well, with Terry playing with the hair in his wig and using the duster to stroke along his ass, making him hard as a rock. Next, with Lana's direction Terry was on all fours on the bed. Ramona had removed the plug and shoved the dildo end of the duster in his ass while Lana filmed the sexual details.

"It needs something" Lana said "But what?" she thought for a moment. "Ramona, shove dick in and out of sissy Terry's ass. Claudia, take that dildo and put it in his mouth" she ordered.

"Yes, Lana" they obediently agreed.

Claudia grabbed a limp dick and sauntered over to Terry. "Open" she commanded. Terry opened his mouth and had the cock shoved inside.

He instantly gagged on it, while tears started to form in his eyes and saliva was drooling from his mouth. Ramona was spanking Terry's rear while shoving the duster dildo in and out of his ass while both girls verbally humiliated him.

"You like this you little sissy whore?" Ramona asked. Terry nodded.

"You're a good little cock sucker, aren't you? Must have experience, maybe you do know a few things about big dicks" Claudia taunted him.

"No...is not authentic" Lana explained. "It needs more..."

The two took the phallic objects out of Terry and the horny sissy hatched an idea. "Um, I can think of something..."

Smash cut to a smirking Claudia and Ramona, fully clothed, but now with strap-on cocks attached to their waists. The two liked the idea and so did Terry. They wasted no time getting into position.

"Ready to get fucked, little girl?" Ramona taunted him.

"I'm gonna make you gag on this dick. Beg for it!" Claudia demanded.

"Yes! Fuck me please, mistresses!"

The two of them instantly rammed their model sissy. Terry accepted the cock to his face while Ramona slowly shoved a few inches at a time until it glided in smoothly into his rectum. She again spanked him.

Lana got the full coverage of Terry being sissified and spit roasted by these two hot chicks who he had humiliated himself to days earlier. But this was the hottest experience of his young life. Indeed, the two fucked Terry in a variety of ways and positions, one of Terry's favorites was being on his side and spreading his cheeks while Claudia dug her dick into his ass while giving him strict instructions. Terry was leaking juices.

Lana enjoyed watching her new model take it in the ass and become a humiliated slut, but she wanted more. She ordered the two to pull their cocks out of Terry once more. He gagged a little bit from being force fed the strap-on.

"Okay girls, now we move on." Lana instructed.

"Can you say: sexy cheerleader?" Ramona asked. Terry smiled.

He was quickly taken out of the maid costume and into his easier to wear cheerleading duds. The girls touched up his makeup and placed he blonde wig on his head. Terry looked at himself in the mirror and damn, he was a pretty hot cheerleader, almost very passable.

"Okay, we pose now" Lana said, adding a new SD card into the camera as well as a new battery.

Terry really got into this one, or perhaps the anxiety of being humiliated was wearing off and it was now purely sexual. Terry would lift his skirt up and shake his ass for the camera and trying to do some cheering poses.

He would lay down on the bed and spread his legs out wide, exposing himself and would crawl seductively towards the camera while Lana got a good angle of the top of his rear end. Terry enjoyed this very much, making a 'come here' motion with his fingers.

"Hope you're ready for more dick" Ramona taunted, greasing up her strap-on with some more lube.

Terry got the butt plug shots out of the way and a few other poses before he was ordered to the bed and accept the girls cocks. He laid on his back and started to suck Ramona's dick while Claudia lifted his legs and removed the butt plug only to immediately replace it with her strap-on.

"Ooh, you're part of the sissy slut squad, huh?" Claudia asked.

"I bet you take a lot of cock in your fuck holes, don't you?" Ramona egged on.

Terry smiled, the dick was taken from his mouth. "Oh yes! I'm a dirty sissy slut!" it was then shoved back in.

"Good! This is what we were looking for!" Lana nodded happily.

After that Terry was ordered to do humiliating poses by each girl before they would nail his ass with her cock, addressing himself as a sissy slut beforehand. It was perfectly humiliating. Then, Terry was forced to straddle Ramona's dick and bounce his ass on it while Claudia stood above and face-fucked him. Ramona was also slapping his balls for good measure.

"Bounce on my cock you little whore!" Ramona said using he free hand to spank his ass from behind.

"Lift up skirt!" Lana demanded, Terry lifted the skirt up with his hands while Lana got some good shots of Terry's feminine cheeks bouncing on Ramona's strap-on dick.

After this, Terry did some more poses, having to lean on the bed and spread his cheeks out with his hands while begging to be fucked by one of the girls. "What you want, Terry?"

"To have my sissy ass fucked!" he begged.

"And?"

"I want my ass fucked every day like the little bitch I am!"

"Good girl" he was then promptly given his wish.

They finished up with the cheerleading outfit, and the final was the prison uniform. Terry was gleefully waiting for this one. He had his makeup redone and had the uniform put on with the red wig. For these poses, Terry would drop the pants and spread his cheeks. He was also given fuzzy pink handcuffs to put on over his wrists to bind them together.

"Ooh, look at this little prison slut" Ramona cooed.

"I bet he'd be used by the entire cellblock" Claudia added.

"What was your crime, slut?" Ramona asked.

"Oh, for having a tiny dick" Terry moaned.

"You're so guilty" Claudia chuckled. "I sentence you to a lifetime of being a sissy anal prison cock slut."

The girls wasted no time, being extra horny from dominating the diminutive Terry. They grabbed him and threw him onto the bed. Claudia threw Terry over her knee and he stuck his ass out in the air, using his bound hands to spread his cheeks. Claudia took a red marker and scribbled BAD GIRL across his cheeks nearly smearing the calligraphy brand. Claudia moved his hands out of the way and began to spank his ass.

"Naughty bitch!"

"Yeah, little tiny dick losers go to sissy jail. Would you like that, slut?" Ramona asked Terry.

"Oh yeah, oh fuck!"

Lana again caught every moment on tape. Claudia continued to spank his rear end sometimes shoving her fingers inside of his asshole while Ramona face fucked him with her strap-on. Eventually they moved on.

They really relished in pounding Terry's ass in the prison uniform. It even got to a point where They tried to insert both dicks inside Terry's hole, making a massive gape when they were finished.

"Look at that pussy take it" Claudia chuckled.

They fucked Terry in a few more positions. He was getting spent and sore, and knew it would be time to clock out soon. After more anal humiliation from the two doms, Lana ordered them to stop, with Terry's red and sore ass sticking up in the air, his hole gaping. Lana handed Ramona a tampon, and she knew what to do.

"We had such a fun time fucking you" she chuckled. "We're gonna stick this in your butt pussy, cause you might bleed a little bit." She inserted the tampon and took out the covering, leaving only the cloth inside of his rectum with the string sticking out.

Terry's cuffs remained on him while the girls were told to lay below his balls with their tongues out, each licking his sack. Lana used her free hand to jerk Terry off and he shot his load onto the girls, who gleefully licked up the droplets that they could.

Finally, they were finished. Terry washed off his makeup and got dressed in his man clothes.

"Bye Terry" Claudia gave him a kiss on the cheek.

"I hope we get to work together soon. You have the best ass" she said giving him a slap before leaving. Lana then presented Terry with a check, this time for an even larger amount. Still sore, he smiled.

"What next?"

Next were many days ahead of location shooting, again typically in back alleyways almost always mere feet from potential passersby on the street. This time Terry would do his pose work but was joined by Claudia and Ramona, dolling him up in makeup and his sissy clothes.

His personal favorite in these situations was the prison uniform.

"Ooh, look at this cute little convict" Claudia would say.

"Let's punish her before returning her back to jail."

Terry was actually sissified on camera with the outfit while the girls were done up in sexy police woman uniforms and then fucked him in the back alleyway. Terry almost hoped someone would happen upon their set and catch a glimpse at him being used.

He would often go home every day, sometimes with a butt plug still in his ass and jerk himself off wishing for the next day of filming to come so he could be humiliated all over again. He was greatly enjoying this form of modeling, especially considering he never thought this was an option. It truly was a new lease on a life he never thought he knew.

Terry did pose after pose for days on end, until Lana told him to start taking breaks, as she had what she hoped was most of what wanted for the website's spread. One day however she finally told him. "Come by tonight, I want to finish your last shoot."

"My last?" A disappointed Terry asked.

"For now. Trust me, I have more work for you. Lots more" she said ominously before smacking his cheek.

Terry nodded. He was ordered to come to Lana's house later that evening around eight o'clock. He waited all day for the occasion. He even avoided masturbating so he could truly enjoy whatever Lana had planned.

He arrived at her manor and just walked in as he was used to going to her home for work by now. "Lana? Hello?" he asked, no answer.

He made his way over to the studio, there was nothing there except the handcuffs and his mask on the bed. Everything seemed as it should but yet something was amiss. Again, Terry called. "Lana? I'm here?"

He noticed the computer was on. Curious, he walked over to it, and saw there was in fact a completed commercial. Terry saw the thumbnail was clearly him shaking his ass on their first day of shooting. He looked around and again saw nobody.

He clicked the play button.

Sensual music began to play as edited shots of the various humiliating photoshoots were played in clips. Terry was impressed by the editing. Writing was scrolled in the lower third: FETISH & FANTASY: unleash your hidden fetishes.

Suddenly, a voice over began to play, it was obviously Lana. "Are you a shemale wishing to unleash your deepest desires? Well, here at Fetish and Fantasy we make that happen. Choose from a variety of our sissy escorts and make your dreams come true."

Terry went wide eyed as the clips turned to him licking his cum off of Lana's office desk. "Our escorts are trained to be obedient submissives and will do any sexual act you so desire."

The shots moved to Terry getting sissified and fucked in various places. "Want to dress them up like a sissy bitch? You may. Abuse their assholes any way you want, it's your dime, your fantasy. Fuck her in public. She's a bad girl."

It then changed to Terry declaring himself a sissy bitch and enjoying taking it up the ass from each of the times they were filming. "Fuck them, cum in them, on them, restrain them, spank them, they'll do it all. Choose from a variety of our many sissy models and always come back for more. We hope to see you soon."

The next shot was Terry as the cheerleader making the come here motion. Then the film faded to the website's banner. "Fetish & Fantasy, an escort service made exclusively for trans women. Unleash your hidden fetishes."

Terry gulped. So this was what it was all about? All of Lana's cryptic warnings made sense to him now. It was a hot proposition but it was definitely too much to take in at once. He couldn't believe how much he let himself be taken in by so quickly...it really was quick and Lana's red flags should have been enough. But, hindsight's 20/20. However, as Terry turned around there stood Lana, in the door way to the studio.

Terry's dick hardened when he saw her. Lana was finally naked, except there was one caveat...dangling between her legs, was a nearly hard cock...which after seeing the video Terry should have been able to guess that. In her hands was a riding crop. "So, now you know."

"This is an escort service?" Terry asked.

"For trans women. Women who want to fuck little sissy bitches like you, Terry." Lana said approaching the boy. "Didn't I tell you, you couldn't handle it?"

"You said it was modeling!"

"This part was. But that is advertisement...advertisement for your ass. If I told you whole story, you simply run, but I tell you just enough to warn you, you still interested...are you, still interested of being sissy escort?"

Terry looked at the advertisement on the computer playing again. His dick did his talking for him as Lana put the end of the crop against his crotch. "That is yes" she snickered. "Now then, all that is left to do is try you out for myself, as final experiment, then you can accept your mistresses. I bet so many line up to fuck you. Now, disrobe" she ordered. Terry was admittedly apprehensive. "Now!" she commanded.

Terry gulped and threw his clothes off, his cock flopping free. Lana knocked her much larger cock into his. "Lay on bed, slut."

Terry hobbled over to the bed while Lana smacked his ass to move it. He flopped down, with his face close to the edge. Lana first used the cuffs to restrain his wrists behind him before putting his mask on. Lana put a Zorro looking mask over her face too. She held her little camcorder and positioned her cock in front of Terry's mouth.

Sure, the thought of signing up to be a sissy escort for shemales seemed like a terrible deal...but why was Terry's dick so hard from it? Did he want this? He clearly wanted Lana. There was something about her commands that was enticing. Maybe this was what he was looking for in his life? Maybe he really didn't care about being a slut at all?

Lana gently pushed her cock inside Terry's mouth and he looked up at the camera, savoring the taste of skin instead of plastic and silicon. Lana got a few inches deeper at a time while recording Terry's humiliation.

"You like my cock?" she asked, Terry nodded. "Good. You will suck many tranny cocks I am sure."

Lana picked up her pace, shoving her larger dick deeper and deeper into Terry's mouth while he tried not to gag on it. His littler dick was so hard from this treatment, he almost couldn't wait for his first client.

"You get mouth nice and loose for cock" she snickered. "We specialize in sissy sluts, so you dress like bitch for clients. You like that, Terry?" he again nodded. "Excellent."

She continued to get her dick deep into Terry's throat. His eyes watered up from having the cock jammed into his esophagus. The girth and hardness was not making it any easier to chug, but he loved it.

He wished he could use his hands to jerk off under the sheets, but alas, they were very bound from the cuffs, making this impossible. Lana further added to the torture by using the riding crop to smack Terry's ass, leaving welts with each pop to his cheeks.

"Yes, shake your sissy ass for me. Good girl" Lana cooed, continuing to pat his cheeks with the crop.

She continued to slop the dick into his mouth, a thick layer of drool was escaping from Terry's lips while Lana fucked his face with her schlong. Terry continued to shake his booty until Lana seemed to be satisfied and took her dick from his mouth.

"Good. Now, I fuck your tight asshole."

She made her way around the bed and hopped on, keeling behind Terry's girly butt. He used his bound hands to spread his cheeks without being told. Lana dropped her riding crop and fingered Terry's tush, using a bottle of lube to drizzle more on his crack.

"Is your sissy butt pussy ready for my cock?"

"Oh yes, Lana!"

"Good!"

Lana slowly inserted her lubed up dick, and shoved the tip inside. She took it back out as Terry moaned loudly, earning him a slap to his ass to shut him up. Lana then tried again. Terry winced as a few inches made it past his sphincter, effectively opening it up.

"There we go" Lana cooed as her dick glided it's way into Terry's rectum. "You're a good little anal whore."

"I'm a little whore. I love it in my ass!" Terry moaned.

Lana picked up her pace a little bit. "You are a slut, you will take cock up your ass. You will do as mistresses command you!"

"Yes!"

Lana shook the bed as she was working up to full speed, still filming from a POV shot of her cock pounding Terry's booty. She used her free hand to grip onto Terry's ass cheeks while she fucked him. "You are weak bitch. You are my sexy model slut! My covergirl!"

"Yes! I'm a little...anal...bitch! Fuck my ass!" Terry begged.

Lana continued her pace, jamming every inch of her cock into Terry's butt, and he winced, his rectum stretching him out from all the fucking. He was still sore from being fucked repeatedly over the course of the past few weeks, but this was ridiculous.

"Yes, we dress you up like little whore to look like slutty girl. You like that?"

"I love it! I love looking like a cock guzzling slut!" Terry begged.

"I know you do. You whore. My model whore! You're mine, slut! You belong to me!"

Terry really liked the sound of that while he drooled onto the fresh sheets of the bed he had been routinely and thoroughly fucked on by Ramona and Claudia. He gushed with glee while getting his ass rammed by his shemale boss.

"You slut. You follow commands only."

"Yes! I do whatever you say" Terry grunted.

"You do not disobey your mistresses, understand?"

"Yes!"

Lana picked up pace again as she was getting close. She grunted, wanting a good final shot of Terry. There was a Sharpie marker on the bed. She quickly uncapped it and took a break from fucking Terry to write: FOR RENT across his cheeks, his calligraphy brand only partially faded.

"I am so close whore. You want my cum on your sexy ass?" Lana asked.

"Oh yes! Fuck! Terry wailed.

Lana pulled her cock out of Terry's hole. "shake your ass, slut!" she demanded.

Terry again did as directed and shook his ass while his hole gaped. Lana gave one final grunt before she shot her load, coating Terry's lower back, then the tops of his cheeks, which she did on both, and let the last dribble down onto his crack. She got the perfect final shot of Terry being thoroughly being sissified. And he wouldn't have it any other way.

"Good. I upload this, then we wait for first client. Clean yourself up, whore!" Lana commanded. She took the cuffs off him.

"Okay" Terry murmured before using his free hands to jerk himself off on the sheets.

Terry went home, very sore from being fucked by his apparent tranny boss and hobbled up to his apartment. He looked wasted, but he was in heaven. All he wanted to do was be a model and turns out he got so much more. He couldn't wait for what was in store for him.

The next morning, Terry laid on his bed, his ass out with two ice packs on them to cushion the blow from a night of fucking. He then got a call from his phone, it was Lana "Hello?" he said a bit nervous.

"You have first client...tonight, meet me at agency at six...oh, your name is Courtney by the way. Don't be late" she warned before hanging up.

Terry threw his face on the bed. A smile crept on his face, ready for the first night of the rest of his life.

**Notes for the Chapter:**

> Any suggestions for Terry, leave them in a form of a comment, you can create a situation, a Tgirl who will date him, or what he's wearing. Thanks for reading!


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